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Search results; Over 1,000 homes in Leeward Settlement

Guest favourite
Guest suite in Leeward Settlement
Handfield's Hideaway Cozy One Bedrm
1 bedroom, 2 beds, 1 private bathroom
17–22 Sept
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4.92 out of 5 average rating, 102 reviews
Guest favourite
Home in Leeward Settlement
Upper East Side Estates Gated Community Leeward
4 bedrooms, 4 king beds, 4 bathrooms
14–19 Sept
4.91 out of 5 average rating, 58 reviews
Guest favourite
Villa in Leeward Settlement
Providenciales Beach Front Villa by Shoreline
3 bedrooms, 3 beds, 3 bathrooms
18–23 Sept
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Villa in Leeward Settlement
Below Deck: Coziest Luxe Villa w/ Firepit & Kayaks
5 bedrooms, 5 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 34 reviews
Guest favourite
Home in Leeward Settlement
Leeward Landing Villa
2 bedrooms, 2 king beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Cottage in Leeward Settlement
Sandpiper Cottage, minutes from the beach
1 bedroom, 1 king bed, 1 bathroom
18–23 Sept
4.89 out of 5 average rating, 158 reviews
Guest favourite
Villa in Leeward Settlement
Luxe Villa-Pool, Putting Green, Bocce, Near Beach
4 bedrooms, 4 beds, 4.5 bathrooms
14–19 Sept
4.9 out of 5 average rating, 30 reviews
Guest favourite
Guest house in Long bay
Villa Kendara~50% 9/25-10/3 ~Beach~Privt~Gate~View
2 bedrooms, 4 beds, 1 bathroom
25–30 Sept
4.94 out of 5 average rating, 97 reviews
Top guest favourite
Cottage in Leeward
Canal Access - SUP - Kayak -Swim. 2BR Guesthouse
2 bedrooms, 2 queen beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Leeward Settlement
25% Off September Great Reviews Walk 2 Beach, Pool
2 bedrooms, 2 beds, 2 bathrooms
18–23 Sept
4.71 out of 5 average rating, 107 reviews
Top guest favourite
Villa in Long Bay Hills
3 Bedrooms Villa Near The Beach
3 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Grace Bay
Follow Your Dreams Villa!
2 bedrooms, 2 queen beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Leeward Settlement
Luxury Paradise 1 Bedroom condo+pool in Grace Bay
1 bedroom, 1 king bed, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 95 reviews
Luxe
Villa in Leeward Settlement
*Brand-new* Villa Terra Blue - Walk to Beach
4 bedrooms, 5 beds, 4.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Flat in Long Bay Hills
Lush 2-Story Villa, Poolside Bliss Near Beach
2 bedrooms, 2 queen beds, 2.5 bathrooms
14–19 Sept
4.83 out of 5 average rating, 30 reviews
Top guest favourite
Home in Leeward Settlement
PERIWINKLE | Charming Island Home|Near to Beach
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.96 out of 5 average rating, 98 reviews
Luxe
Home in Leeward Settlement
CanalFront Retreat 9BR9.5BA Luxury w/ Private Dock
9 bedrooms, 9 beds, 9.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Leeward Settlement
Sapphire Sands –Lotus Villa #3 Privacy, Pool, BBQ
3 bedrooms, 3 beds, 3.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 30 reviews
Villa in Leeward Settlement
Piccolo Ponte | 3 BR Canal Front | Pool & Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
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